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1,1’-Binaphthalene-2-α-arylmethanol-2’-ols (Ar-BINMOLs) with Axial and sp3-Central Chirality：A Novel Chiral Ligands for Catalytic Asymmetric Transformations
Received date: 2014-03-25
Revised date: 2014-04-17
Online published: 2014-05-06
Supported by
Project supported by the National Natural Science Foundation of China (No. 21173064) and the Zhejiang Provincial Natural Science Foundation of China (No. R14B030003).
1-(2-Hydroxynathalen-1-yl)naphthalene-2-ol (BINOL) and its derivatives have been used widely as chiral ligands in asymmetric catalysis. Recently, we have found that the simple axial chiral monoalkylated BINOLs could be converted into synthetically useful and enantiomerically pure 1,1'-binaphthalene-2-α-arylmethanol-2'-ols (Ar-BINMOLs) with axial and sp3-central chirality through the axial-to-central chirality transfer of [1,2]-Wittig rearrangement. At present, the catalytic application of Ar-BINMOLs in asymmetric catalysis has been revealed by our and Yus's groups. In this account, the progress in the field of BINOL and its derivatives will also be reported concisely in the article, and the Ar-BINMOLs and its derivatives as new chiral ligands for application in asymmetric catalysis would be summarized detailedly.
Zheng Longsheng , Song Tao , Xu Liwen . 1,1’-Binaphthalene-2-α-arylmethanol-2’-ols (Ar-BINMOLs) with Axial and sp3-Central Chirality：A Novel Chiral Ligands for Catalytic Asymmetric Transformations[J]. Chinese Journal of Organic Chemistry, 2014 , 34(7) : 1255 -1267 . DOI: 10.6023/cjoc201403053
[1] Ager, D. J.; East, M. B. Asymmetric Synthetic Methodology, CRC, Boca Raton, FL, 1996.
[2] Ojima, I. Catalytic Asymmetric Synthesis, John Wiley & Sons, New Jersey, 2004.
[3] Gawley, R. E.; Aubé, J. Principles of Asymmetric Synthesis, 2nd ed, Elsevier, 2012.
[4] Ding, K. L.; Han, Z. B.; Wang, Z. Chem. Asian J. 2009, 4, 32.
[5] Yong, T. P.; Jacobsen, E. N. Science 2003, 299, 1691.
[6] Kagan, H. B. In Asymmetric Synthesis, Ed.: Morrison, J. D., Academic Press, New York, 1985.
[7] Cram, D. J.; Cram, J. M. Acc. Chem. Res. 1978, 11, 8.
[8] Noyori, R.; Tomino, I.; Tanimoto, Y. J. Am. Chem. Soc. 1979, 101, 3129.
[9] Chen, Y.; Yekta, S.; Yudin, A. K. Chem. Rev. 2003, 103, 3155.
[10] Brunel, J. M. Chem. Rev. 2007, 107, 1.
[11] Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375.
[12] Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2004, 43, 468.
[13] Lee, J. Y.; Miller, J. J.; Hamilton, S. S.; Sigman, M. S. Org. Lett. 2005, 7, 1837.
[14] (a) Gao, G.; Gu, F. L.; Jiang, J. X.; Jiang, K. Z.; Sheng, C. Q.; Xu, L. W. Chem. Eur. J. 2011, 17, 2698.
(b) Gao, G.; Bai, X. F.; Yang, H. M.; Jiang, J. X.; Lai, G. Q.; Xu, L. W. Eur. J. Org. Chem. 2011, 5039.
(c) Gao, G.; Bai, X. F.; Li, F.; Zheng, L. S.; Zheng, Z. J.; Lai, G. Q.; Jiang, K. Z.; Li, F. W.; Xu, L. W. Tetrahedron Lett. 2012, 53, 2164.
(d) Zheng, L. S.; Jiang, K. Z.; Deng, Y.; Bai, X. F.; Gao, G.; Gu, F. L.; Xu, L. W. Eur. J. Org. Chem. 2013, 4, 748.
[15] (a) Wu, T. R.; Shen, L. X.; Chong, J. M. Org. Lett. 2004, 6, 2701;
(b) Blay, G.; Fernández, I.; Pedro, R. J.; Vila, C. Org. Lett. 2007, 9, 2601.
(c) Blay, G.; Fernández, M.; Muñoz, C.; Pedro, J. R.; Vila, C. Eur. J. Org. Chem. 2013, 1902.
(d) Huang, G. C.; Yin, Z. S.; Zhang, X. G. Chem. Eur. J. 2013, 19, 11992.
[16] (a) Lingenfelter, D. S.; Helgeson, R. C.; Cram, D. J. J. Org. Chem. 1981, 46, 393.
(b) Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253.
(c) Simonsen, K. B.; Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1998, 63, 7536.
(d) Zhang, Z. G.; Dong, Z. B.; Li, J. S. Chirality 2010, 22, 820.
(e) Lin, L.; Zhang, J. L.; Ma, X. J.; Fu, X.; Wang, R. Org. Lett. 2011, 13, 6410.
[17] Milburn, R. R.; Hussain, S. M. S.; Prien, O.; Ahmed, Z.; Snieckus, V. Org. Lett. 2007, 9, 4403.
[18] (a) Wang, Q.; Chen, S. Y.; Yu, X. Q.; Pu, L. Tetrahedron 2007, 63, 4422.
(b) Yue, Y.; Turlington, M.; Yu, X. Q.; Pu, L. J. Org. Chem. 2009, 74, 8681.
[19] Maruoka, K.; Itoh, T.; Araki, Y.; Shirasaka, T.; Yamamoto, H. Bull. Chem. Soc. Jpn.1988, 8, 2975.
[20] Gribkov, D. V.; Hultzsch, K. C.; Hampel, F. J. Am. Chem. Soc. 2006, 128, 3748.
[21] Kodama, H.; Ito, J.; Hori, K.; Ohta, T.; Furukawa, I. J. Organomet. Chem. 2000, 603, 6.
[22] Beckendorf, S.; Mancheño, O. G. Synthesis 2012, 2162.
[23] Casas, J.; Baeza, A.; Sansano, J. M.; Nájera, C.; Saá, J. M. Tetrahedron: Asymmetry 2003, 14, 197.
[24] Qin, Y. C.; Liu, L.; Sabat, M.; Pu, L. Tetrahedron 2006, 62, 9335.
[25] Gou, S. H.; Zhou, X.; Wang, J.; Liu, X. H.; Feng, X. M. Tetrahedron Lett. 2008, 64, 2864.
[26] Nájera, C.; Sansano, J. M.; Saá, J. M. Eur. J. Org. Chem. 2009, 2385.
[27] Li, H.; Da, C. S.; Xiao, Y. H.; Li, X.; Su, Y. N. J. Org. Chem. 2008, 73, 7398.
[28] Guo, Q. S.; Liu, B.; Lu, Y. N.; Jiang, F. Y.; Song, H. B.; Li, J. S. Tetrahedron: Asymmetry 2005, 16, 3667.
[29] (a) Matsui, K.; Takizawa, S.; Sasai, H. J. Am. Chem. Soc. 2005, 127, 3680.
(b) Matsui, K.; Tanaka, K.; Horii, A.; Takizawa, S.; Sasai, H. Tetrahedron: Asymmetry 2006, 17, 578.
[30] Qian, C.; Zhu, C.; Huang, T. J. Chem. Soc., Perkin Trans. 1 1998, 2131.
[31] (a) Vogl, E. M.; Matsunaga, S.; Kanai, M.; Iida, T.; Shibasaki, M. Tetrahedron Lett.1998, 39, 7917.
(b) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Adv. Synth. Catal. 2002, 344, 3.
(c) Shibasaki, M.; Matsunaga, S. J. Organomet. Chem. 2006, 691, 2089.
(d) Shibasaki, M.; Matsunaga, S. Chem. Soc. Rev. 2006, 35, 269.
[32] Hashimoto, T.; Omote, M.; Maruoka, K. Org. Biomol. Chem. 2008, 6, 2263.
[33] (a) Sasai, H.; Arai, R.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
(b) Sasai, H.; Tokugana, T.; Shizue, W.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem.1995, 60, 7388.
[34] Kadiri, M. Y. E.; Framery, E.; Andrioletti, B. Tetrahedron Lett. 2012, 53, 6335.
[35] Bunzen, J.; Bruhn, T.; Bringmann, G.; Lützen, A. J. Am. Chem. Soc. 2009, 131, 3621.
[36] Tian, Y.; Chan, K. S. Tetrahedron Lett. 2000, 41, 8813.
[37] Mikami, K.; Ueki, M.; Matsumoto, Y.; Terada, M. Chirality 2001, 13, 541.
[38] Enev, V.; Ewers, C. L. J.; Harre, M.; Nikische, K.; Mohr, J. T. J. Org. Chem. 1997, 62, 7092.
[39] Kiyooka, S.; Tsutsui, T.; Kira, T. Tetrahedron Lett. 1996, 37, 8903.
[40] (a) Marshall J. A. In Comprehensive Organic Synthesis, Vol. 3, Eds.: Trost, B. M.; Fleming, I., Pergamon, Oxford, 1991, p. 975.
(b) Tomooka, K.; Yamamoto, H.; Nakai, T. Liebigs Ann. Recl. 1997, 1275.
[41] Wittig, G.; Löhmann, L. Justus Liebigs Ann. Chem. 1942, 550, 260.
[42] (a) Nakai, T.; Mikami, K. Chem. Rev. 1986, 86, 885.
(b) Kita-mura, M.; Hirokawa, Y.; Maezaki, N. Chem. Eur. J. 2009, 15, 9911.
(c) Sasaki, M.; Ikemoto, H.; Kawahata, M.; Yamaguchi, K.; Takeda, K. Chem. Eur. J. 2009, 15, 4663.
(d) Giampietro, N. C.; Wolf, J. P. Angew. Chem., Int. Ed. 2010, 49, 2922.
[43] Selected examples: (a) Tomooka, K.; Yamamoto, H.; Nakai, T. J. Am.Chem. Soc. 1996, 118, 3317;
(b) Barluenga, J.; Faňanás, F. J.; Sanz, R.; Marcos, C.; Trabada, M. Org. Lett. 2002, 4, 1587.
[44] Santos, L. S. Reactive Intermediates, Wiley-VCH, Weinheim, 2010.
[45] Gao, G. M.S. Thesis, Hangzhou Normal University, Hangzhou, 2012 (in Chinese).
(高广, 硕士论文, 杭州师范大学, 杭州, 2012.)
[46] (a) Somanathan, R.; Flores-Lopez, L.Z.; Montalvo-Gonza-lez, R.; Chavez, D.; Parra-Hake, M.; Auirre, G. Mini-Rev. Org. Chem. 2010, 7, 10.
(b) Zhong, J. C.; Hou, S. C.; Qian, Q. H.; Yin, M. M.;Na, R. S.; Zheng, B.; Li, Z. Y.; Liu, S. Z.; Wang, M. Chem. Eur. J. 2009, 15, 3069.
(c) Lombardo, M.; Chia-rucci, M.; Trombini, C. Chem. Eur. J. 2008, 14, 11288.
(d) Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757.
[47] (a) Yoshioka, M.; Kawakita, T.; Ohno, M. Tetrahedron Lett. 1989, 30, 1657.
(b) Takahashi, H.; Kawakita, T.; Yoshioka, M.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 7095.
[48] (a) Schmidt, B.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 1321.
(b) Zhang, F. Y.; Yip, C. W.; Cao, R.; Chan, A. S. C. Tetrahedron: Asymmetry 1997, 8, 585.
(c) Balsells, J.; Walsh, P. J. J. Am. Chem.Soc. 2000, 122, 3250.
(d) Balsells, J.; Walsh, P. J. J. Am. Chem.Soc. 2000, 122, 1802.
(e) Hatano, M.; Miyamoto, T.; Ishihara, K. Adv. Synth. Catal. 2005, 347, 1561.
(f) Tanaka, T.; Sano, Y.; Hayashi, M. Chem. Asian J. 2008, 3, 1465.
(g) Gou, S. H.; Judeh, Z. M. A. Tetrahedron Lett. 2009, 50, 281.
(h) Zhang, Z. G.; Dong, Z. B.; Li, J. S. Chirality 2010, 22, 820.
(i) Adreu, A. R.; Pereira, M. M.; Bayon, J. C. Tetrahedron 2010, 66, 743.
(j) Von Ronn, R.; Christoffers, J. Tetrahedron Lett. 2011, 67, 334.
[49] (a) Fernández-Mateos, E.; Maciá, B.; Ramón, D. J.; Yus, M. Eur. J. Org. Chem. 2011, 6851.
(b) Fernández-Mateos, E.; Maciá, B.; Yus, M. Eur. J. Org. Chem. 2012, 3732.
(c) Fernández-Mateos, E.; Maciá, B.; Yus, M. Tetrahedron: Asymmetry 2012, 23, 789.
(d) Fernández-Mateos, E.; Maciá, B.; Yus, M. Adv. Synth. Catal. 2013, 355, 1249.
[50] Li, F.; Zheng, Z. J.; Shang, J. Y.; Jiang, K. Z.; Lai, G. Q.; Jiang, J. X.; Xu, L. W. Chem. Asian J. 2012, 7, 2008.
[51] Li, F.; Li, L.; Yang, W.; Zheng, L. S.; Zheng, Z. J.; Jiang, K. Z.; Lu, Y. X.; Xu, L. W. Tetrahedron Lett. 2013, 54, 1584.
[52] Zheng, L. S.; Li, L.; Yang, K. F.; Zheng, Z. J.; Xiao, X. Q.; Xu, L. W. Tetrahedron Lett. 2013, 69, 8777.
[53] Yamamoto, H.; Zhou, F. Synfacts 2014, 10, 56.
[54] Ye, F.; Zheng, Z. J.; Deng, W. H.; Zheng, L. S.; Deng, Y.; Xia, C. G.; Xu, L. W. Chem. Asian J. 2013, 8, 2242.
[55] Song, T.; Zheng, L. S.; Ye, F.; Deng, W. H.; Wei, Y. L.; Jiang, K. Z.; Xu, L. W. Adv. Synth. Catal. 2014, 356, 1708.
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